ES2423795T3 - Procedimiento de cristalización de eritromicina - Google Patents
Procedimiento de cristalización de eritromicina Download PDFInfo
- Publication number
- ES2423795T3 ES2423795T3 ES09822979T ES09822979T ES2423795T3 ES 2423795 T3 ES2423795 T3 ES 2423795T3 ES 09822979 T ES09822979 T ES 09822979T ES 09822979 T ES09822979 T ES 09822979T ES 2423795 T3 ES2423795 T3 ES 2423795T3
- Authority
- ES
- Spain
- Prior art keywords
- erythromycin
- dichloromethane
- crystals
- solution
- organic solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 title claims abstract description 157
- 229960003276 erythromycin Drugs 0.000 title claims abstract description 86
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002425 crystallisation Methods 0.000 title description 3
- 230000008025 crystallization Effects 0.000 title description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 159
- 239000013078 crystal Substances 0.000 claims abstract description 42
- 238000001953 recrystallisation Methods 0.000 claims abstract description 10
- 239000011877 solvent mixture Substances 0.000 claims abstract description 8
- 239000000725 suspension Substances 0.000 claims abstract description 6
- 229930006677 Erythromycin A Natural products 0.000 claims description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 230000002906 microbiologic effect Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- PGNYNCTUBKSHHL-UHFFFAOYSA-N 2,3-diaminobutanedioic acid Chemical compound OC(=O)C(N)C(N)C(O)=O PGNYNCTUBKSHHL-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000001514 detection method Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KKCMGMIPHDNPQL-YZPBMOCRSA-N (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;2-hyd Chemical compound CC(O)C(O)=O.O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 KKCMGMIPHDNPQL-YZPBMOCRSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810225310 | 2008-10-29 | ||
| CN2008102253108A CN101724000B (zh) | 2008-10-29 | 2008-10-29 | 一种红霉素的结晶方法 |
| PCT/CN2009/001204 WO2010048786A1 (zh) | 2008-10-29 | 2009-10-29 | 一种红霉素的结晶方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2423795T3 true ES2423795T3 (es) | 2013-09-24 |
Family
ID=42128202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09822979T Active ES2423795T3 (es) | 2008-10-29 | 2009-10-29 | Procedimiento de cristalización de eritromicina |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8436154B2 (xx) |
| EP (1) | EP2341056B1 (xx) |
| JP (1) | JP5596695B2 (xx) |
| CN (1) | CN101724000B (xx) |
| AU (1) | AU2009310267B2 (xx) |
| ES (1) | ES2423795T3 (xx) |
| HK (1) | HK1153202A1 (xx) |
| HR (1) | HRP20130516T1 (xx) |
| PL (1) | PL2341056T3 (xx) |
| SI (1) | SI2341056T1 (xx) |
| WO (1) | WO2010048786A1 (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102199179B (zh) * | 2011-03-14 | 2013-09-11 | 金泳霖 | 一种净化并回收利用发酵法生产红霉素料液的方法 |
| CN102942607A (zh) * | 2012-11-28 | 2013-02-27 | 宁夏启元药业有限公司 | 一种复合溶剂结晶红霉素的方法 |
| CN105622690A (zh) * | 2016-03-25 | 2016-06-01 | 伊犁川宁生物技术有限公司 | 一种高纯度红霉素a的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2864817A (en) * | 1955-09-01 | 1958-12-16 | Lilly Co Eli | Process for crystallization of erythromycin |
| US4751220A (en) * | 1986-12-19 | 1988-06-14 | E. R. Squibb & Sons, Inc. | Crystalline salts of [3S(Z)]-2[[[1-(2-amino-4-thiazolyl)-2-[[2,2-dimethyl-4-oxo-1-(sulfooxy)-3-azetidinyl]amino]-2-oxoethylidene]-amino]oxy]acetic acid |
| RO99792B1 (ro) * | 1987-12-28 | 1990-06-29 | Institutul De Cercetari Chimico-Farmaceutice | Procedeu de cristalizare a eritromicinei |
| RO103274A2 (en) * | 1988-12-28 | 1991-12-09 | Inst De Cercetari Chimico Farm | Recovery method of erythromycin from mother-waters |
| JP2007204490A (ja) * | 1995-08-03 | 2007-08-16 | Chugai Pharmaceut Co Ltd | エリスロマイシン誘導体の製造方法 |
| JP2005522470A (ja) * | 2002-04-03 | 2005-07-28 | ハンミ ファーム． シーオー．， エルティーディー． | アジスロマイシンの製造方法及びそれに用いられる９−デオキソ−９ａ−アザ−９ａ−ホモエリスロマイシンＡの結晶性水和物 |
| CN1219788C (zh) | 2003-03-27 | 2005-09-21 | 华东理工大学 | 红霉素盐制备红霉素的动态控制结晶方法 |
-
2008
- 2008-10-29 CN CN2008102253108A patent/CN101724000B/zh active Active
-
2009
- 2009-10-29 WO PCT/CN2009/001204 patent/WO2010048786A1/zh active Application Filing
- 2009-10-29 EP EP09822979.2A patent/EP2341056B1/en active Active
- 2009-10-29 US US13/063,933 patent/US8436154B2/en active Active
- 2009-10-29 JP JP2011533513A patent/JP5596695B2/ja active Active
- 2009-10-29 AU AU2009310267A patent/AU2009310267B2/en active Active
- 2009-10-29 PL PL09822979T patent/PL2341056T3/pl unknown
- 2009-10-29 ES ES09822979T patent/ES2423795T3/es active Active
- 2009-10-29 SI SI200930687T patent/SI2341056T1/sl unknown
-
2011
- 2011-07-14 HK HK11107335.6A patent/HK1153202A1/xx unknown
-
2013
- 2013-06-11 HR HRP20130516AT patent/HRP20130516T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2341056A4 (en) | 2012-03-14 |
| EP2341056B1 (en) | 2013-05-29 |
| JP2012506877A (ja) | 2012-03-22 |
| SI2341056T1 (sl) | 2013-09-30 |
| CN101724000A (zh) | 2010-06-09 |
| US20110172402A1 (en) | 2011-07-14 |
| HRP20130516T1 (xx) | 2013-07-31 |
| PL2341056T3 (pl) | 2013-10-31 |
| CN101724000B (zh) | 2012-05-30 |
| WO2010048786A1 (zh) | 2010-05-06 |
| HK1153202A1 (en) | 2012-03-23 |
| JP5596695B2 (ja) | 2014-09-24 |
| US8436154B2 (en) | 2013-05-07 |
| AU2009310267A1 (en) | 2010-05-06 |
| AU2009310267B2 (en) | 2013-06-20 |
| EP2341056A1 (en) | 2011-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PT103661A (pt) | Processo de preparação de minociclina base cristalina | |
| JP2010184925A (ja) | セフジニルの新規な結晶形 | |
| ES2706314T3 (es) | Método para la producción de praziquantel y precursores del mismo | |
| ES2423795T3 (es) | Procedimiento de cristalización de eritromicina | |
| RU2387656C2 (ru) | Способ получения гидробромида галантамина | |
| RU2011141429A (ru) | Улучшенный способ получения меропенема с применением цинкового порошка | |
| CN102617383A (zh) | 索法地尔晶型、制备方法及包含索法地尔晶体的无菌粉末 | |
| ES2791295T3 (es) | Procedimiento para purificar ácido ferúlico y/o sales del mismo | |
| AR081267A1 (es) | Procedimiento de obtencion de la forma cristalina a del febuxostat | |
| CN106008554A (zh) | 一种头孢曲松钠无菌粉的制备方法及产品 | |
| ES2455518T3 (es) | Purificación de mupirocina | |
| ES2602171T3 (es) | Proceso de preparación de tiocianato de eritromicina | |
| CN105859747B (zh) | 一种适于工业化生产的盐酸头孢吡肟的制备方法 | |
| CN110114333B (zh) | 赖氨酸乙酰水杨酸盐·甘氨酸颗粒的改进合成 | |
| ES2318520T3 (es) | Proceso mejorado para la fabricacion de mitazapina. | |
| KR20090121270A (ko) | 미르타자핀의 제조 방법 | |
| CN110372729B (zh) | 一种氟氧头孢钠的精制方法 | |
| CA2881958C (en) | Pharmaceutical formulations containing 3-(4-cinnamyl-1-piperazinyl) amino derivatives of 3-formylrifamycin sv and 3-formylrifamycin s and a process of their preparation | |
| CN105873935B (zh) | 结晶的β-内酰胺酶抑配制品 | |
| JP2009007257A (ja) | ケルセチン含有植物材料を用いたケルセチンスルホン酸の製造方法 | |
| KR100512870B1 (ko) | 7α-메톡시세팔로스포린 유도체 나트륨염 7수화물의제조방법 | |
| ES2208110B1 (es) | Formas cristalinas de acido fusidico y procedimientos para su obtencion. | |
| RU2260012C1 (ru) | Способ кристаллизации азитромицина дигидрата | |
| RU2272041C1 (ru) | Способ выделения натриевой соли оксациллина из водных или водно-органических сред | |
| JP2013213004A (ja) | オランザピンの製造方法 |